Director at PayPal vs VP at unknown startup
9YOE Non-eng, non-product TC @ Square: $1M+ (Joined at IPO), L7/Director level Sick of my boss and no other team has an immediate need for my skills as it’s fairly niche. I’m leaving to take time off regardless. Two offers: 1) Director at PayPal, priority area for the company, high visibility. Annual TC: ————— $225K Base 25% Bonus $150K RSU annually $100K Signing Bonus I heard they do 50% RSU refreshers annually. High potential for future growth given importance of role. Very aligned and great rapport with VP. 2) VP at unknown startup. I’m confident it will either IPO or get acquired within 2yrs given the recent C level hires they’ve done, but it’s a very old business that recently got its shit together, somewhat. Reporting to the CEO. Annual TC: ————— $225K Base 25% Bonus ??? Options $25K Signing Bonus Vague promises of generous options grants annually. Reasonable outcomes would mean Annual TC of 650-750K, highest projected outcome is TC of 1.5-2M if all the stars align and my acceleration triggers kick in. There is a downside scenario where the company continues to stay private after 2yrs, in which case my annual TC stays around 285 (base and bonus) I know a bunch of people at PayPal, and it’s comfortable work IMO. The VP role is a step up in title but they need a lot of work in everything including culture. The people are definitely not top tier, and I’m not super passionate about the field they’re in, but the mandate of the role is very interesting. What would you do?
If you have a good cushion, I’d go for the startup gig. If it works, you’re a step up to VP somewhere more stable afterwards. If it works REALLY well, you’re a CEO candidate not in a distant future. On hindsight, PayPal will give you some leeway to build into a VP career without startup concerns. Bottom line for me: Startup to fast track career; PayPal to live the humdrum life.
I do have a good cushion, even after my eye watering tax bill! Fair points.
Wait around for a better startup gig. Doing a startup gig if you're not passionate about it will make you miserable. At this point all you're getting is the VP title.
I don’t want to burn too much cash, and I have a family and giant mortgage to support, so I’m eager to plan out my next move. I will continue to search, but let’s say these are the two roles available.
Then I'd go with PayPal and spend a year or two looking around for the perfect startup opportunity
Seems like your heart is at PayPal but the money is at Start-up
I think so, and I’m trying to justify it as if I can either get promoted to a Sr Dir role within 2yrs if I’m coming in on the higher end of the scale, or if the initiative they’re hiring me for is successful, then I have an incredible amount of cachet in my narrow specialization, which can lead to a future VP role.
I would say take the VP role. You will automatically get access to the VC network and if things don’t work out, they’ll find you a VP role elsewhere. It’s all about who you know in the Valley.
VC angle is interesting. I’ve heard that before but never worked in a true startup so I have to guess. The board exposure will open up future opps?
Yes it will. Especially if you meet with them on a regular basis to talk about your product strategy, which you definitely will because it’s a start up. Even if things don’t end up working out between you and the CEO, the board members will see your intelligence and bring you into another start up instead
Take PayPal. Like you mentioned if the company doesn’t IPO in the next 2 years then you could be taking a major hit on comp.
Director at paypal is professionally nothing, it does not require a profession, nor knowledge, nor talent, you just have to be "high up" somewhere. directors fired from PayPal in the 20% HR cut are still unemployed. It's a good retirement job if you're a good politician and can navigate and manage up.
What is the 20% HR cut ?
Neither. Keep looking. If you aren't sure, it's not worth going.
As a Director at PayPal, I'd say go for it. Esp if you're going to be in San Jose and working on a high visibility initiative. If long term you want to go startup, wait for the right one - it doesn't look like you're super enthu about the one you're considering.
Looks like you are ~30 years old. Most of the Directors and above at PP are 40+. So, keep that also in mind!
This is a good point. If most of the directors are in their 40s, they may not appreciate that OP got to a director level without “paying his dues“. He may just be shut out and face a lot of political battles.
Follow your passion
They’re both interesting in their own regard. I think the core business of PayPal is more interesting but the roles themselves are equally cool.